A short and efficient route from tetrahydrothiophene to thieno[2,3-d][1,3,2]dithiazolium salts |
| |
Authors: | Lidia S KonstantinovaVadim V Popov Andrey V LalovLjudmila V Mikhalchenko Vadim P GultyaiOleg A Rakitin |
| |
Institution: | N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, 119991 Moscow, Russia |
| |
Abstract: | A synthesis of thieno2,3-d]1,3,2]dithiazolium salts from commercial tetrahydrothiophene has been developed. The reaction of thieno2,3-f]1,2,3,4,5]pentathiepin with LiAlH4 in THF at −15 °C, after treatment with acetyl chloride, led to 2,3-(bisacetylthio)thiophene in high yield. Bis(acetylthio)thiophene reacted with sulfuryl chloride and then trimethylsilyl azide was added to afford a 1,3,2-dithiazolium chloride which was converted into a soluble tetrafluoroborate. Electrolytic reduction under controlled potential yielded a thieno2,3-d]1,3,2]dithiazolyl radical which was characterized by EPR in frozen methylene dichloride. |
| |
Keywords: | Sulfur-nitrogen heterocycles Fused 1 3 2-dithiazoles 1 2 3 4 5-Pentathiepins Electrochemical reduction EPR spectroscopy |
本文献已被 ScienceDirect 等数据库收录! |
|